Mailbag: To Bring Or Not To Bring Girls To NOLA, Deleting Pics Of Your Ex From IG, And Sex With Your Best Friend


Welcome to the PGP Mailbag, wherein I will answer questions from you, our readers. Send your questions to All topics welcome.

Yo Dillon,

Big fan of your work. So this past summer I was put up in a hotel by my work for the whole summer and now have hella Marriott points that are burning a hole in my pocket. A trip to New Orleans for New Years looks to be the move, but my best boy and I are debating on whether to open up the inquiry to the girlfriends or rest of the dudes.

Also, any hole in the wall places we should go to that aren’t popular? We’ll try any and everything possible in a 2 day span.

You and your “best boy” should make this a guys’ trip. You can absolutely take your girlfriends and have an awesome time, but New Orleans is a dirty place where weird shit happens. It’s better suited for the guys. If you want to hit the craps table at 3 a.m. or see if Rick’s Cabaret is as dirty as you’ve heard about, it’s easier to make happen when the better half is a few states over.

My off-the-beaten-path (it’s on Bourbon actually) recommendation is Lafitte’s Blacksmith Shop. It’s the oldest bar in New Orleans (the building is from 1761) and the structure has some interesting history to it. It’s rumored to even be haunted. Hole-in-the-wall feel that opens to the street. Very cool, New Orleans-y spot.

I ended a 4 year relationship this summer. Obviously there are a lot of pictures of us online. It feels like deleting them would be like erasing 4 years of my life. I’m over the relationship and I think I’m in a place now where I’m grateful that it happened, I know that it just wasnt working anymore and I’m ready to move on. Recently started to talking to someone new and with that comes following each other on social media. I’m worried about what he might think of all the pictures of my ex. Am I overreacting? I feel like deleting them makes it seem like I’m trying to hide something. What should I do?

Unless the relationship was toxic and the pictures conjure up bad memories, I think it’s a bad move to delete them. That would be erasing traces of a pretty big chunk of your life. I wouldn’t worry about what the new guy will think. I mean, he knows you’ve dated before. Like you said, it can even be perceived as a red flag if your picture timeline suddenly jumps from 2013 to 2017 with few pictures sprinkled in between.

So my better half lives in LA, and I’m planning on moving out there some time next summer, say June/July timeframe, but my lease ends in January. My options right now are either move home for those 4 months or sign a lease, knowing I’m going to have to break it. Currently I’m thinking moving home is the right call because of the $4000+ I’ll be saving on rent and utilities alone, money that can go straight to an overpriced rock a year or so later, or in reality a nice vacation and college football gambling money. Part of me also realizes moving back home after only a year isn’t quite the respectable move.

Any knowledge of friends doing the same/any input you can provide would be useful. Note that my parents are gone every weekend to the lake and living at home didn’t bother me for the year and a half I did it after college.

Moving home for the four months is definitely the move here. Signing a lease for four months should only be on the table if you don’t have another place to stay in the interim. The extra moving alone (assuming you already have a room set up for you at your parents’ house) even makes it not worth it.

I used to daydream about moving back home for three or four months just to stack paper. You actually have a legit reason to do it. Do it. Save that money.

Hi Dillon,

I’d like to first say that I love your columns and always find this one particularly helpful and interesting. I wish I didn’t need this advice right now but I do. A year ago, I moved to live in the same town as my boyfriend. After two years of dating, he broke up with me because he doesn’t see us ending up together and he fell out of love with me. Not only does getting dumped by the one you think you’re going to marry absolutely suck but I am stuck in this town where all of my friends here are also his mutual friends. I have a good job but I’m not sure if that’s enough for me to stick around. I don’t want to rush into dating immediately but I worry that I wouldn’t be able to do it here because it’s a relatively small town where his ties run deep. I’m 26 so I’m in a place where I could afford to start over but I don’t have a clue where I would move if I did leave. All of this happened this past week so I’m trying to not make any immediate decisions but I’m wondering what you would you do in this case. I’m kind of grasping for any semblance of plan on how to move on from this and bounce back into my best self. Any advice from you or other readers would be greatly appreciated…

It sounds like you need a fresh start somewhere else. I’m sure you’re still feeling down from the breakup, but once that begins to fade away you should look at this as an opportunity to do something big and different. It’s pretty fucking exciting when you’re in the right mindset, actually. You can live anywhere you want, do whatever you want, start to date again, all that fun stuff.

If I’m you, I start putting my résumé out there in cool cities just to see what happens. You’re in no rush so take your time and be picky.


Whats poppin fam, glad to hear you’ve had a successful transition into #citylife. I myself have made the move to the DT area and it has been lit af to say the very least. Anywho, let’s dive in:

So about a year ago, per any season opener tradition, I decided to get absolutely 115% blackout inebriated. Come to find out the next day I banged one of my best friends. Whoopsies.

Fast forward to now and we’re still really tight pals who hang (read: bang) on the reg. Here’s the kicker– in the entire year that we’ve been hooking up on the low we have never ever not once talked about or acknowledged it. So there’s a good chance both of us are fucking psychopaths.

It’s been understood that this is very open, but lately he’s been wayyy protective/intimate and gets irritated when I talk to other guys. Unfortunately, I have the same emotional capacity as Bill Belichick and recently he tried to get a reaction out of me via blatantly deflating his balls in someone else. Which worked. Long story short: shit is escalating in both camps and on a fucking collision course with either Exclusivity or Ruined Friendship and both sound terrifying.

Obviously the days of this idiotic (yet impressively executed) system are numbered. You’re a big communication guy (everybody knows this), but I don’t even know what my end game would be in that convo and am worried that once it’s all out in the open the friendship is gonna go up in flames.

Do I just create some space instead? It seems like a bitch move but distance sounds like my only other option here.

Sorry for the long read. The four cups of coffee sustaining my existence have got me keyboard happy. Thanks in advance.

— A friend no longer benefiting

“Long story short: shit is escalating in both camps and on a fucking collision course with either Exclusivity or Ruined Friendship and both sound terrifying.”

Basically, yeah.

You both need to decide, either collectively or on your own, if these feelings are worth pursuing. If they are, cool, maybe see if something is there. Go on real, actual dates and you’ll figure out pretty quickly if this could turn into a relationship. If you both agree that basic friendship is right path to take, however, you should stop having sex. Like now. I know that’s not as fun as having the sex, but not having it is the way to preserve the friendship, if it’s even salvageable at this point.

It’s very difficult for two people to maintain a friendship when at least one wants to sleep with the other. And when sex does occur, that friendship is on its deathbed. This story has been written a million times. They all pretty much end the same way.


Longtime Toucher, first time writing in.

Most people have their first initial and last name as their company email, but I recently saw a guy who just had his last name and my mind was blown. I couldn’t decide if it was a power move. Then I realized your email is just your first name, crazy stuff. I know your office is more relaxed, which could explain the first name email. What would you suggest, and would it depend on what type of job the person has?

Keep up the great work,

I haven’t put any thought into this until reading your email. I always assumed first name @ ______ was commonplace for work emails. Am I wrong?

Here’s an interesting, topical tidbit. My last name is so rare that was available to me many years ago. It got spammed into oblivion and I don’t know how to recover the password, unfortunately, but I always thought that was nuts.


The more questions I receive, the better this series is going to be, so send me your Mailbag questions to and please put “Mailbag” in the subject line.

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Dillon Cheverere

Dillon Cheverere is the Vice President of Media for Grandex, Inc. Dillon graduated (BBA) with a GPA sitting in the meaty part of the bell curve, not lagging behind, but not trying to show off, either. Golf is his game now. He's long off the tee but can't putt for shit. Email:

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